CN101434551B - Method for synthesizing monoethanolamine - Google Patents
Method for synthesizing monoethanolamine Download PDFInfo
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- CN101434551B CN101434551B CN2008102427010A CN200810242701A CN101434551B CN 101434551 B CN101434551 B CN 101434551B CN 2008102427010 A CN2008102427010 A CN 2008102427010A CN 200810242701 A CN200810242701 A CN 200810242701A CN 101434551 B CN101434551 B CN 101434551B
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- mea basf
- monoethanolamine mea
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- monoethanolamine
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Abstract
The invention discloses a synthesis method of monoethanolamine, pertaining to the technical field of organic chemical synthesis. Hydroxyacetonitrile is adopted for carrying out reaction with hydrogen under the presence of a catalyst to obtain the monoethanolamine. Compared with the prior art, the technical proposal has the advantages of full transformation (more than 81 percent) and high yield (more than 70 percent).
Description
Technical field
The present invention relates to a kind of synthetic method of Monoethanolamine MEA BASF, belong to the organic chemistry synthesis technical field.
Background technology
Monoethanolamine MEA BASF has another name called the 2-monoethanolamine, and molecular formula is NH
2CH
2CH
2OH.
The main at present synthetic Monoethanolamine MEA BASF of oxyethane that adopts promptly reacts acquisition by oxyethane and ammonia under silver catalyst and high-temperature and high-pressure conditions, reaction equation is as follows:
The first step side reaction:
The second step side reaction:
This method is owing to meeting in reaction process produces diethanolamine, two kinds of by products of trolamine, so transformation efficiency lower (about 30%), because transformation efficiency is low, so yield is also low.
Summary of the invention
The object of the present invention is to provide a kind of synthetic method that transforms the Monoethanolamine MEA BASF complete, that yield is high.
The objective of the invention is to reach like this, a kind of synthetic method of Monoethanolamine MEA BASF, it is to adopt hydroxyacetonitrile and hydrogen to react in the presence of catalyzer to obtain Monoethanolamine MEA BASF.
The mass percent concentration of hydroxyacetonitrile of the present invention is any concentration.
The mass percent concentration of hydroxyacetonitrile of the present invention is 50～100%.
The mol ratio of hydroxyacetonitrile of the present invention and hydrogen is 1: 2～30.
The mol ratio of hydroxyacetonitrile of the present invention and hydrogen is 1: 2～10.
The temperature of reaction of reaction of the present invention is 60～200 ℃.
The reaction times of reaction of the present invention is 2～18 hours.
The mass percent of hydroxyacetonitrile of the present invention and catalyzer is 1: 0.001～0.005.
Catalyzer of the present invention is to be the nickel aluminum-copper alloy powder of carrier loaded Al and Cu with Ni, the mass percentage content of Ni 〉=90% wherein, the mass percentage content of Al≤7%, the mass percentage content of Cu≤4%.
Compared with the prior art technical scheme disclosed in this invention has the advantage that transforms complete (more than 81%) and yield height (more than 70%).
Embodiment:
The chemical equation of the inventive method is:
The following examples do not constitute the restriction to the present invention program, though for example only lift and nickel aluminum-copper alloy powder for catalyzer, do not repel other similarly or claim the catalyzer of equivalence, Nickel Aluminium Alloy Powder for example, nickel-aluminum-molybdenum alloy powder etc.
Embodiment 1:
With mass percent concentration is that 5% hydroxyl acetonitrile aqueous solution 579g and catalyzer are that (mass percent of Ni is 98% for the nickel aluminum-copper alloy powder 0.144g of carrier loaded Al and Cu with Ni promptly, the mass percent of Al is 0.5%, the mass percent of Cu is 1.5%) add in the 1000mL hydrogenation reaction kettle, under agitation, add 30g hydrogen from the hydrogenation mouth of hydrogenation reaction kettle, the intensification control reaction temperature is 200 ℃, insulation reaction 18h, when no longer changing, pressure stops heating, cooling, blowing, feed liquid is transferred in the 1000mL there-necked flask, underpressure distillation gets the pure product 42.8g of Monoethanolamine MEA BASF.Monoethanolamine MEA BASF transformation efficiency 81.5%, Monoethanolamine MEA BASF yield are 70.16%.
Embodiment 2:
With mass percent concentration is that 10.2% hydroxyl acetonitrile aqueous solution 558.9g and catalyzer are that the nickel aluminum-copper alloy powder 0.057g (mass percent of Ni is 99%, the mass percent of Al is 0.7%, the mass percent of Cu be 0.3%) of carrier loaded Al and Cu adds in the 1000mL hydrogenation reaction kettle with Ni promptly, under agitation, add 22g hydrogen from the hydrogenation mouth, the intensification control reaction temperature is 80 ℃, insulation reaction 16h, when no longer changing, pressure stops heating, cooling, blowing, feed liquid is transferred in the 1000mL neck bottle, underpressure distillation gets the pure product 44g of Monoethanolamine MEA BASF.Monoethanolamine MEA BASF transformation efficiency 81.5%, Monoethanolamine MEA BASF yield are 72.13%.
Embodiment 3:
With mass percent concentration is that 20.5% hydroxyl acetonitrile aqueous solution 278g and catalyzer are that the nickel aluminum-copper alloy powder 0.085g (mass percent of Ni is 97%, the mass percent of Al is 1.4%, the mass percent of Cu be 1.6%) of carrier loaded Al and Cu adds in the 1000mL hydrogenation reaction kettle with Ni promptly, under agitation, add 16g hydrogen from the hydrogenation mouth, the intensification control reaction temperature is 90 ℃, insulation reaction 14h, pressure stops heating when no longer changing, cooling, blowing, feed liquid is transferred in the 1000mL there-necked flask, underpressure distillation gets the pure product 47g of Monoethanolamine MEA BASF.Monoethanolamine MEA BASF transformation efficiency 86.5%, Monoethanolamine MEA BASF yield are 77.05%.
Embodiment 4:
With mass percent concentration is that 30% hydroxyl acetonitrile aqueous solution 190g and catalyzer are that the nickel aluminum-copper alloy powder 0.114g (mass percent of Ni is 95.1%, the mass percent of Al is 4%, the mass percent of Cu be 0.9%) of carrier loaded Al and Cu adds in the 1000mL hydrogenation reaction kettle with Ni promptly, under agitation, add 10.4g hydrogen from the hydrogenation mouth, the intensification controlled temperature is 140 ℃, insulation reaction 10h, pressure stops heating when no longer changing, cooling, blowing, feed liquid is transferred in the 1000mL there-necked flask, underpressure distillation gets the pure product 49.8g of Monoethanolamine MEA BASF.Monoethanolamine MEA BASF transformation efficiency 87.5%, Monoethanolamine MEA BASF yield are 81.64%.
Embodiment 5:
With mass percent concentration is that 50% hydroxyl acetonitrile aqueous solution 114g and catalyzer are that the nickel aluminum-copper alloy powder 0.142g (mass percent of Ni is 94.4%, the mass percent of Al is 3.6%, the mass percent of Cu be 2%) of carrier loaded Al and Cu adds in the 1000mL hydrogenation reaction kettle with Ni promptly, under agitation, add 8g hydrogen from the hydrogenation mouth, the intensification control reaction temperature is 160 ℃, insulation reaction 8h, when no longer changing, pressure stops heating, cooling, blowing, feed liquid is transferred in the 1000mL there-necked flask, underpressure distillation gets the pure product 52g of Monoethanolamine MEA BASF.Monoethanolamine MEA BASF transformation efficiency 93.5%, Monoethanolamine MEA BASF yield are 85.25%.
Embodiment 6:
With mass percent concentration is that 70% hydroxyl acetonitrile aqueous solution 81.5g and catalyzer are that (mass percent of Ni is 92.6% for the nickel aluminum-copper alloy powder 0.199g of carrier loaded Al and Cu with Ni promptly, the mass percent of Al is 6.6%, the mass percent of Cu is 0.8%) add in the 1000mL hydrogenation reaction kettle, under agitation, add 5.2g hydrogen from the hydrogenation mouth, control reaction temperature is 200 ℃, insulation reaction 6h, when no longer changing, pressure stops heating, cooling, blowing, feed liquid is transferred in the 1000mL there-necked flask, underpressure distillation gets the pure product 59.1g of Monoethanolamine MEA BASF.Monoethanolamine MEA BASF transformation efficiency 98.5%, Monoethanolamine MEA BASF yield are 96.89%.
Embodiment 7:
With mass percent concentration is that 83% hydroxyl acetonitrile aqueous solution 69g and catalyzer are that the nickel aluminum-copper alloy powder 0.229g (mass percent of Ni is 91%, the mass percent of Al is 5%, the mass percent of Cu be 4%) of carrier loaded Al and Cu adds in the 1000mL hydrogenation reaction kettle with Ni promptly, under agitation, add 4.8g hydrogen from the hydrogenation mouth, the intensification control reaction temperature is 150 ℃, insulation reaction 4h, when no longer changing, pressure stops heating, cooling, blowing, feed liquid is transferred in the 1000mL there-necked flask, underpressure distillation gets the pure product 52.6g of Monoethanolamine MEA BASF.Monoethanolamine MEA BASF transformation efficiency 92.5%, Monoethanolamine MEA BASF yield are 86.23%.
Embodiment 8:
With mass percent concentration is that 90% hydroxyl acetonitrile aqueous solution 64g and catalyzer are that (mass percent of Ni is 91.5% for the nickel aluminum-copper alloy powder of carrier loaded Al and Cu with Ni promptly, the mass percent of Al is 7%, the mass percent of Cu is 1.5%) 0.259g adds in the 1000mL hydrogenation reaction kettle, under agitation, add 4.4g hydrogen from the hydrogenation mouth, the intensification control reaction temperature is 180 ℃, insulation reaction 15h, when no longer changing, pressure stops heating, cooling, blowing, feed liquid is transferred in the 1000mL there-necked flask, underpressure distillation gets the pure product 45.8g of Monoethanolamine MEA BASF.Monoethanolamine MEA BASF transformation efficiency 84.5%, Monoethanolamine MEA BASF yield are 75.08%.
Embodiment 9:
With mass percent concentration is that 99.8% hydroxyl acetonitrile aqueous solution 57.2g and catalyzer are that nickel aluminum-copper alloy powder (mass percent of Ni is 90%, the mass percent of Al is 6%, the mass percent of Cu the be 4%) 0.285g of carrier loaded Al and Cu adds in the 1000mL hydrogenation reaction kettle with Ni promptly, under agitation, add 60g hydrogen from the hydrogenation mouth, the intensification control reaction temperature is 80 ℃, insulation reaction 10h, pressure stops heating when no longer changing, cooling, blowing, feed liquid is transferred in the 1000mL neck bottle, underpressure distillation gets the pure product 51.2g of Monoethanolamine MEA BASF.Monoethanolamine MEA BASF transformation efficiency 87.2%, Monoethanolamine MEA BASF yield are 83.93%.
Embodiment 10:
With mass percent concentration is that 58% hydroxyl acetonitrile aqueous solution 98.28g and catalyzer are that (mass percent of Ni is 92.4% for the nickel aluminum-copper alloy powder of carrier loaded Al and Cu with Ni promptly, the mass percent of Al is 6.8%, the mass percent of Cu is 0.8%) 0.189g adds in the 1000mL hydrogenation reaction kettle, under agitation, add 51g hydrogen from the hydrogenation mouth, the intensification control reaction temperature is 150 ℃, insulation reaction 15h, when no longer changing, pressure stops heating, cooling, blowing, feed liquid is transferred in the 1000mL there-necked flask, underpressure distillation gets the pure product 52.8g of Monoethanolamine MEA BASF.Monoethanolamine MEA BASF transformation efficiency 91.4%, Monoethanolamine MEA BASF yield are 86.56%.
Embodiment 11:
With mass percent concentration is that 52% hydroxyl acetonitrile aqueous solution 109.62g and catalyzer are that (mass percent of Ni is 94.4% for the nickel aluminum-copper alloy powder of carrier loaded Al and Cu with Ni promptly, the mass percent of Al is 5.4%, the mass percent of Cu is 0.2%) 0.285g adds in the 1000mL hydrogenation reaction kettle, under agitation, add 39g hydrogen from the hydrogenation mouth, the intensification control reaction temperature is 120 ℃, insulation reaction 12h, when no longer changing, pressure stops heating, cooling, blowing, feed liquid is transferred in the 1000mL there-necked flask, underpressure distillation gets the pure product 53.1g of Monoethanolamine MEA BASF.Monoethanolamine MEA BASF transformation efficiency 92.3%, Monoethanolamine MEA BASF yield are 87.05%.
Be that the nickel aluminum-copper alloy powder of carrier loaded Al and Cu is preferred but not what be limited to is to adopt that to deceive the trade mark that eastern catalyzer Manufacturing Co., Ltd produces by the Suzhou City, Jiangsu Province, China be Raney's nickel 2122 with Ni described in the above embodiment 1 to embodiment 11.
Claims (8)
1. the synthetic method of a Monoethanolamine MEA BASF, it is characterized in that it is to adopt hydroxyacetonitrile and hydrogen to react to obtain Monoethanolamine MEA BASF in the presence of catalyzer, described catalyzer is to be the nickel aluminum-copper alloy powder of carrier loaded Al and Cu with Ni, the mass percentage content of Ni 〉=90% wherein, the mass percentage content of Al≤7%, the mass percentage content of Cu≤4%.
2. the synthetic method of a kind of Monoethanolamine MEA BASF according to claim 1 is characterized in that described hydroxyacetonitrile is the solution form, and its mass percent concentration is any concentration.
3. the synthetic method of a kind of Monoethanolamine MEA BASF according to claim 2, the mass percent concentration that it is characterized in that described hydroxyacetonitrile is 50～100%.
4. the synthetic method of a kind of Monoethanolamine MEA BASF according to claim 1, the mol ratio that it is characterized in that described hydroxyacetonitrile and hydrogen is 1: 2～30.
5. the synthetic method of a kind of Monoethanolamine MEA BASF according to claim 4, the mol ratio that it is characterized in that described hydroxyacetonitrile and hydrogen is 1: 2～10.
6. the synthetic method of a kind of Monoethanolamine MEA BASF according to claim 1, the temperature of reaction that it is characterized in that described reaction is 60～200 ℃.
7. the synthetic method of a kind of Monoethanolamine MEA BASF according to claim 1, the reaction times that it is characterized in that described reaction is 2～18 hours.
8. the synthetic method of a kind of Monoethanolamine MEA BASF according to claim 1, the mass percent that it is characterized in that described hydroxyacetonitrile and catalyzer is 1: 0.001～0.005.
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| CN2008102427010A CN101434551B (en) | 2008-12-13 | 2008-12-13 | Method for synthesizing monoethanolamine |
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| CN2008102427010A CN101434551B (en) | 2008-12-13 | 2008-12-13 | Method for synthesizing monoethanolamine |
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| CN101434551A CN101434551A (en) | 2009-05-20 |
| CN101434551B true CN101434551B (en) | 2011-01-12 |
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Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103271238B (en) * | 2013-05-10 | 2014-04-02 | 中国科学院亚热带农业生态研究所 | Preparation method of feed additive mono ethanol amine and application |
| CN108203387B (en) * | 2018-01-23 | 2021-01-15 | 万华化学集团股份有限公司 | Method for preparing monoethanolamine by hydrogenation of hydroxyacetonitrile |
| CN112608244B (en) * | 2020-12-22 | 2022-11-11 | 山东华鲁恒升化工股份有限公司 | Novel method for preparing monoethanolamine |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1023401C (en) * | 1990-07-02 | 1994-01-05 | 浙江大学 | Process for liquid-liquid tube reaction for production of ethanolamine |
| CN1077882C (en) * | 1993-11-02 | 2002-01-16 | 株式会社日本触媒 | Process for preparation for alkanolamine, catalyst used in process for preparation of catalyst |
| CN1911899A (en) * | 2006-08-18 | 2007-02-14 | 临安善才科技有限公司 | Preparation method of 2-amino-2-methyl-1-propanol |
| CN101033193A (en) * | 2007-04-11 | 2007-09-12 | 浙江大学 | Method of synthesizing 2-aminopropanol |
-
2008
- 2008-12-13 CN CN2008102427010A patent/CN101434551B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1023401C (en) * | 1990-07-02 | 1994-01-05 | 浙江大学 | Process for liquid-liquid tube reaction for production of ethanolamine |
| CN1077882C (en) * | 1993-11-02 | 2002-01-16 | 株式会社日本触媒 | Process for preparation for alkanolamine, catalyst used in process for preparation of catalyst |
| CN1911899A (en) * | 2006-08-18 | 2007-02-14 | 临安善才科技有限公司 | Preparation method of 2-amino-2-methyl-1-propanol |
| CN101033193A (en) * | 2007-04-11 | 2007-09-12 | 浙江大学 | Method of synthesizing 2-aminopropanol |
Non-Patent Citations (2)
| Title |
|---|
| J.William Lown et al.Synthesis and Reactions of Deuterated.《J.org.Chem》.1981,第46卷(第12期),2479-2482. * |
| 马良晓.2008102427010.《STN检索报告》.2010, * |
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Owner name: JIANGSU YUANYANG PHARMACEUTICAL CO., LTD. Free format text: FORMER OWNER: JIANGSU YUANYANG CHEMISTRY CO., LTD. Effective date: 20120329 |
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Effective date of registration: 20120329 Address after: 215531, Jiangsu, Changshou City province Tong Industrial Park, 204 National Road, 948.5 kilometers Patentee after: Jiangsu Yuanyang Pharmaceutical Co.,Ltd. Address before: 215531, Jiangsu, Changshou City province Tong Industrial Park, 204 National Road, 934.5 kilometers Patentee before: Jiangsu Yuanyang Chemistry Co., Ltd. |